Issue Date: November 10, 2008
Fluorocarbon Solvent Ups Metathesis Yields
Replacing common organic solvents with aromatic fluorocarbons can boost yields in complex olefin metathesis reactions catalyzed by commercial ruthenium catalysts, according to researchers in Poland (Chem. Commun., DOI: 10.1039/b816567j). The commercially available catalysts sometimes provide low yields in olefin metathesis procedures used for synthesizing or derivatizing natural products and biologically active compounds. As a result, some researchers focus on designing more effective catalysts, whereas others simply use higher concentrations of the commercial catalysts. Karol Grela of the Polish Academy of Sciences, in Warsaw, and coworkers report that yields obtained with commercial catalysts can be dramatically enhanced by running reactions in fluorinated solvents. For example, in ring-closing reactions on a malonate compound, switching from dichloroethane to perfluorotoluene while otherwise maintaining identical reaction conditions led to an 18-fold increase in the yield of the cyclic olefin. Fluorinated solvents also enhanced yields in ring-closing reactions of pentaene vitamin compounds, the researchers note. They also observed similar improvements in cross-metathesis reactions of steroids and other compounds of pharmaceutical interest. The team is currently exploring the origin of the enhanced catalytic activity.
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